1,2-Diiodoethane → 6-(2-Iodooxazol-5-yl)isoquinoline

HRID 598825Notes

Reaction equation

[O:1]1[C:5]([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[CH:12]=[N:11][CH:10]=[CH:9]3)=[CH:4][N:3]=[CH:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[I:26]CCI.S([O-])([O-])(=O)=S.[Na+].[Na+]>CCOCC.C1COCC1>[I:26][C:2]1[O:1][C:5]([C:6]2[CH:7]=[C:8]3[C:13](=[CH:14][CH:15]=2)[CH:12]=[N:11][CH:10]=[CH:9]3)=[CH:4][N:3]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a 150 mL round-bottomed flask was added 6-(oxazol-5-yl)isoquinoline (0.50 g, 2.55 mmol) and THF (20 mL), and the resulting reaction mixture was stirred at −78° C. The solution was then treated dropwise via syringe with lithium bis(trimethylsilyl)amide (1.0 M solution in THF (3.06 mL, 3.06 mmol)), and the reaction was stirred for 1 hour at −78° C. A THF solution of 1,2-diiodoethane (0.826 g, 2.93 mmol) was then added dropwise, and the reaction was allowed to warm to room temperature for 1 hour. The reaction was then poured into a 1:1 mixture of ether and saturated sodium thiosulfate. Approximately 100 mg was purified on a Varian HPLC, 5-70% ACN in water, 60 minutes run, to give 68 mg of pure compound. LCMS (API-ES) m/z (%): 323 (100%, M++H); 1H NMR (400 MHz, CDCl3) δ ppm 9.19 (s, 1H) 8.51 (d, J=5.67 Hz, 1H) 8.01 (s, 1H) 7.96 (d, J=8.61 Hz, 1H) 7.73 (dd, J=8.61, 1.57 Hz, 1H) 7.63 (d, J=5.67 Hz, 1H) 7.42 (s, 1H).

Workup

customthe resulting reaction mixture
stirringthe reaction was stirred for 1 hour at −78° C
temperatureto warm to room temperature for 1 hour
customApproximately 100 mg was purified on a Varian HPLC, 5-70% ACN in water, 60 minutes

Sources & evidence

ORD record: ord-71383570686a4ba8bd1aae7c6398eadd
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897619B2

Reaction notes

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